<span style="color:black">Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived </span><em style="color:black">meso</em><span style="color:black">-Tetraarylporphyrin</span>
Porphyrins were identified some years ago as a promising, easily accessible, and tunable class of organic photoredox catalysts, but a systematic study on the effect of the electronic nature and of the position of the substituents on both the ground-state and the excited-state redox potentials of the...
| Autores: | , , , , , , , , , , |
|---|---|
| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2024 |
| País: | España |
| Institución: | Universidad de Barcelona |
| Repositorio: | Dipòsit Digital de la UB |
| OAI Identifier: | oai:diposit.ub.edu:2445/218389 |
| Acceso en línea: | https://hdl.handle.net/2445/218389 |
| Access Level: | acceso abierto |
| Palabra clave: | Porfirines Electroquímica Porphyrins Electrochemistry |
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<span style="color:black">Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived </span><em style="color:black">meso</em><span style="color:black">-Tetraarylporphyrin</span>Dardouri, N. E.Hrichi, S.Torres, PolChaabane-Banoues, R.Sorrenti, AlessandroRoisnel, T.Turowska-Tyrk, I.Babba, I.Crusats i Aliguer, JoaquimMoyano i Baldoire, AlbertNasri, H.PorfirinesElectroquímicaPorphyrinsElectrochemistryPorphyrins were identified some years ago as a promising, easily accessible, and tunable class of organic photoredox catalysts, but a systematic study on the effect of the electronic nature and of the position of the substituents on both the ground-state and the excited-state redox potentials of these compounds is still lacking. We prepared a set of known functionalized porphyrin derivatives containing different substituents either in one of the meso positions or at a β-pyrrole carbon, and we determined their ground- and (singlet) excited-state redox potentials. We found that while the estimated singlet excited-state energies are essentially unaffected by the introduction of substituents, the redox potentials (both in the ground- and in the singlet excited-state) depend on the electron-withdrawing or electron-donating nature of the substituents. Thus, the presence of groups with electron-withdrawing resonance effects results in an enhancement of the reduction facility of the photocatalyst, both in the ground and in the excited state. We next prepared a second set of four previously unknown meso-substituted porphyrins, having a benzoyl group at different positions. The reduction facility of the porphyrin increases with the proximity of the substituent to the porphine core, reaching a maximum when the benzoyl substituent is introduced at a meso position.MDPI2024info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://hdl.handle.net/2445/218389Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésReproducció del document publicat a: https://doi.org/10.3390/molecules29153689Molecules, 2024, vol. 29https://doi.org/10.3390/molecules29153689cc-by (c) Dardouri, N. E. et al., 2024http://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/2183892026-05-27T06:46:51Z |
| dc.title.none.fl_str_mv |
<span style="color:black">Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived </span><em style="color:black">meso</em><span style="color:black">-Tetraarylporphyrin</span> |
| title |
<span style="color:black">Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived </span><em style="color:black">meso</em><span style="color:black">-Tetraarylporphyrin</span> |
| spellingShingle |
<span style="color:black">Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived </span><em style="color:black">meso</em><span style="color:black">-Tetraarylporphyrin</span> Dardouri, N. E. Porfirines Electroquímica Porphyrins Electrochemistry |
| title_short |
<span style="color:black">Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived </span><em style="color:black">meso</em><span style="color:black">-Tetraarylporphyrin</span> |
| title_full |
<span style="color:black">Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived </span><em style="color:black">meso</em><span style="color:black">-Tetraarylporphyrin</span> |
| title_fullStr |
<span style="color:black">Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived </span><em style="color:black">meso</em><span style="color:black">-Tetraarylporphyrin</span> |
| title_full_unstemmed |
<span style="color:black">Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived </span><em style="color:black">meso</em><span style="color:black">-Tetraarylporphyrin</span> |
| title_sort |
<span style="color:black">Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived </span><em style="color:black">meso</em><span style="color:black">-Tetraarylporphyrin</span> |
| dc.creator.none.fl_str_mv |
Dardouri, N. E. Hrichi, S. Torres, Pol Chaabane-Banoues, R. Sorrenti, Alessandro Roisnel, T. Turowska-Tyrk, I. Babba, I. Crusats i Aliguer, Joaquim Moyano i Baldoire, Albert Nasri, H. |
| author |
Dardouri, N. E. |
| author_facet |
Dardouri, N. E. Hrichi, S. Torres, Pol Chaabane-Banoues, R. Sorrenti, Alessandro Roisnel, T. Turowska-Tyrk, I. Babba, I. Crusats i Aliguer, Joaquim Moyano i Baldoire, Albert Nasri, H. |
| author_role |
author |
| author2 |
Hrichi, S. Torres, Pol Chaabane-Banoues, R. Sorrenti, Alessandro Roisnel, T. Turowska-Tyrk, I. Babba, I. Crusats i Aliguer, Joaquim Moyano i Baldoire, Albert Nasri, H. |
| author2_role |
author author author author author author author author author author |
| dc.subject.none.fl_str_mv |
Porfirines Electroquímica Porphyrins Electrochemistry |
| topic |
Porfirines Electroquímica Porphyrins Electrochemistry |
| description |
Porphyrins were identified some years ago as a promising, easily accessible, and tunable class of organic photoredox catalysts, but a systematic study on the effect of the electronic nature and of the position of the substituents on both the ground-state and the excited-state redox potentials of these compounds is still lacking. We prepared a set of known functionalized porphyrin derivatives containing different substituents either in one of the meso positions or at a β-pyrrole carbon, and we determined their ground- and (singlet) excited-state redox potentials. We found that while the estimated singlet excited-state energies are essentially unaffected by the introduction of substituents, the redox potentials (both in the ground- and in the singlet excited-state) depend on the electron-withdrawing or electron-donating nature of the substituents. Thus, the presence of groups with electron-withdrawing resonance effects results in an enhancement of the reduction facility of the photocatalyst, both in the ground and in the excited state. We next prepared a second set of four previously unknown meso-substituted porphyrins, having a benzoyl group at different positions. The reduction facility of the porphyrin increases with the proximity of the substituent to the porphine core, reaching a maximum when the benzoyl substituent is introduced at a meso position. |
| publishDate |
2024 |
| dc.date.none.fl_str_mv |
2024 |
| dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.none.fl_str_mv |
https://hdl.handle.net/2445/218389 |
| url |
https://hdl.handle.net/2445/218389 |
| dc.language.none.fl_str_mv |
Inglés |
| language_invalid_str_mv |
Inglés |
| dc.relation.none.fl_str_mv |
Reproducció del document publicat a: https://doi.org/10.3390/molecules29153689 Molecules, 2024, vol. 29 https://doi.org/10.3390/molecules29153689 |
| dc.rights.none.fl_str_mv |
cc-by (c) Dardouri, N. E. et al., 2024 http://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess |
| rights_invalid_str_mv |
cc-by (c) Dardouri, N. E. et al., 2024 http://creativecommons.org/licenses/by/4.0/ |
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openAccess |
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application/pdf |
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MDPI |
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MDPI |
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Articles publicats en revistes (Química Inorgànica i Orgànica) reponame:Dipòsit Digital de la UB instname:Universidad de Barcelona |
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Universidad de Barcelona |
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Dipòsit Digital de la UB |
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Dipòsit Digital de la UB |
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